Nitriles: Conjugate addition and cyclization

ORGN 142

Subrahmanyam Gudipati, gudipatis@duq.edu and Fraser F Fleming. Bayer school of natural and environmental sciences, Duquesne university, 600 Forbes Avenue, Pittsburgh, PA 15282

Conjugate addition to unsaturated nitriles are notoriously difficult, preventing conjugate addition-alkylation-annulation strategies. This presentation describes an  intermolecular conjugate addition to cyclic unsaturated nitriles in aqueous media. The radicaloid conditions allow functionalized nucleophile bearing a pendant electrophile for subsequent intramolecular alkylation which provides a fundamentally new annulation strategy with cyclic alkene nitriles through sequential conjugate addition-cuprate cyclization.